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MCM-41 Heterogenized Chiral Amines as Base Catalysts for Enantioselective Michael Reaction
Authors:A. Corma  S. Iborra  I. Rodríguez  M. Iglesias  F. Sánchez
Affiliation:(1) Instituto de Tecnología Química, UPV-CSIC, Universidad Politécnica de Valencia, Avda. de los Naranjos s/n, 46022 Valencia, Spain;(2) Instituto de Química Orgánica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain
Abstract:Cinchonidine and cinchonine have been grafted onto pure silica MCM-41. It has been shown that both supported alkaloids are active catalysts for the Michael addition of ethyl 2-oxocyclopentanecarboxylate and methyl vinyl ketone, anchored cinchonidine being more active and enantioselective than anchored cinchonine. The study of the influence of the polarity of the solvent and reaction temperature on the optical induction shows that there is not a direct correlation between solvent polarity and enantioselectivity, and the maximum optical yield was obtained between 278 and 273 K.
Keywords:enantioselective Michael reaction  MCM-41 heterogenized cinchonine  heterogenized cinchonidine  solid chiral base catalyst  enantioselective catalysts
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